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Akinwande began his career with Millwall at the age of seven, and remained at the club for nine years. After his release by Millwall, Akinwande signed for Conference Premier side Dartford in the summer of 2013.[4]

Akinwande made three brief substitute appearances in three different cup competitions during his first season at Dartford. He first appeared in their 1–0 win against Charlton Athletic in the Kent Senior Cup on 17 October 2013,[5] and then, after making his Dartford league debut as a late substitute in their 1–0 home defeat against Forest Green on 12 April 2014,[6] Akinwande was promoted to Dartford's first-team squad ahead of the 2014–15 season.[7]

During the summer of 2014, Akinwande had trials with Brentford and Crystal Palace. He first lined up for Brentford a pre-season friendly in late July, and played a part in their 2–1 victory over Maidenhead United for the club's Development Squad.[8] A few days later, he was included in the Crystal Palace under-21 squad in a 3–2 victory at Dulwich Hamlet for another friendly.[9]

Remaining with Dartford for the 2014–15 season, Akinwande was one of four players loaned to Isthmian League Division One South club Walton Casuals.[10] Despite failing to make an appearance for the club during his short spell, Akinwande was loaned to Isthmian League Premier Division side Leatherhead for a month in November 2014.[11] He played for the club on six occasions during the month, four times in the FA Trophy, once in the Isthmian League Cup, and once in the Surrey Senior Cup.[12]

Akinwande left Fisher at the end of the season to join Isthmian League Division One North side Maldon & Tiptree.[17] He scored on his debut for the Jammers on 8 August 2015 in new managerDavid Wright's first game in charge as they won 2–1 against Phoenix Sports.[18] He scored four goals in his first five games for the club, going on to score eleven goals in 15 league games and twelve in 18 games in all competitions.[19]

Akinwande's performances for Maldon & Tiptree earned him a trial with League One side Colchester United's Academy where he featured in two games for the Development Squad in November 2015.[20] He signed a professional contract with the club until the end of the 2015–16 season, remaining in the Development Squad.[21] In February 2016, Akinwande was named in the first-team squad for the first time. He was handed shirt number 16 and was an unused substitute in Colchester's game against Bury on 20 February.[22] He was handed his professional debut on 12 March when manager Kevin Keen named Akinwande in his starting eleven to face Wigan Athletic at the Colchester Community Stadium. He played the first 45-minutes in the 3–3 draw before being replaced by Gavin Massey.[23] He was offered a new contract by Colchester at the end of the season.[24][25] He agreed a new one-year deal with Colchester on 7 July 2016.[26]

Akinwande made a loan return to Maldon & Tiptree on 3 February 2017, signing for an initial one month.[30] He made his second debut
for the Jammers on 4 February in their 1–0 defeat at Brightlingsea Regent,[31] and scored his first goal in his second match during a 4–0 win over Thurrock on 11 February.[32]